Diisopropylamine → 2-(Methylthio)-4-[(3-nitrophenyl)ethynyl]pyrimidine

HRID 1159873ノート

反応式

HRID 1159873 の反応式
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.C(NC(C)C)(C)C.[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=1)#[CH:18]>C1COCC1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:9][S:8][C:4]1[N:3]=[C:2]([C:18]#[C:17][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)[CH:7]=[CH:6][N:5]=1

参加物

7

反応物 3

HCID 7912DiisopropylamineHCID 76432Benzene, 1-ethynyl-3-nitro-HCID 38589014-Iodo-2-(methylthio)pyrimidine

生成物 1

HCID 595114132-(Methylthio)-4-[(3-nitrophenyl)ethynyl]pyrimidine収率 98.6%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
25 °C

実験手順

4-Iodo-2-(methylthio)pyrimidine (39.7 g, 0.157 mol) and diisopropylamine (44.2 mL, 0.315 mol) are dissolved in dry THF (720 mL) and argon gas is bubbled through the solution for 20 min. Copper(I) iodide (2.99 g, 14.3 mmol) and bis(triphenylphosphine)palladium dichloride (5.51 g, 7.85 mmol) are added and then 1-ethynyl-3-nitrobenzene (25.4 g, 0.173 mol) in dry THF (100 mL) is added dropwise over about 30 min with the temperature being maintained at about 25° C. Following complete addition, the mixture is stirred at rt for overnight. The mixture is filtered and washed with THF. The filtrate is concentrated under reduced pressure. The residue is washed with EtOAc/MeOH to give pale-yellow solid (42 g).

後処理

  1. customargon gas is bubbled through the solution for 20 min
  2. additionaddition
  3. filtrationThe mixture is filtered
  4. washwashed with THF
  5. concentrationThe filtrate is concentrated under reduced pressure
  6. washThe residue is washed with EtOAc/MeOH

出典と根拠

ORDレコード
ord-bf6200784b3c445ba41e7483d3b50551
出典データセット
uspto-grants-2010_10
特許番号
US07812022B2

反応ノート

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